ALPHA-LACTAM INTERMEDIATES IN BASE-PROMOTED REACTIONS OF O-SULFONYLATED HYDROXAMIC ACIDS WITH NUCLEOPHILES

被引：25

作者：

HOFFMAN, RV

NAYYAR, NK

CHEN, WT

机构：

[1] Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 12期

关键词：

D O I：

10.1021/ja00065a011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of N-(sulfonyloxy) amides with bases proceeds by initial formation of an alpha-lactam intermediate. A primary kinetic deuterium isotope effect, k(H)/k(D) = 2.17, a leaving group effect, beta(lg)CH3 = 0.50, and nucleophilic trapping all confirm that the alpha-lactam is produced in the rate-determining step. Ring opening to an ion pair and nucleophilic addition to C-2 produce 2-substituted amide products.

引用

页码：5031 / 5034

页数：4

共 24 条

[1]

AOYAMA T, 1991, SYNTHESIS-STUTTGART, P1163

[2]

BALDON CM, 1982, J CHEM SOC CHEM COMM, P1402

[3] REACTIONS OF AMINES .9. REARRANGEMENT OF N-T-BUTYL-N-CHLOROAMIDES [J].